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CAS No.: | 865-21-4 |
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Name: | Vinblastine |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C46H58N4O9 |
Molecular Weight: | 810.988 |
Synonyms: | Vinblastine(7CI);(+)-Vinblastine;1H-Indolizino[8,1-cd]carbazole-5-carboxylic acid,4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-,methyl ester, [3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-;Rozevin;VLB;Valban;Vinblastin;Vincaleucoblastin;Vincaleucoblastine;[3aR-[3aa,4b,5b,5ab,9(3R*,5S*,7R*,9S*),10bR*,13aa]]-Methyl 4-(acetyloxy)-3a-ethyl-9-[5-ethyl-1,4,5,6,7,8,9,10-octahydro-5-hydroxy-9-(methoxycarbonyl)-2H-3,7-methanoazacycloundecino[5,4-b]indol-9-yl]-3a,4,5,5a,6,11,12,13a-octahydro-5-hydroxy-8-methoxy-6-methyl-1H-indolizino[8,1-cd]carbazole-5-carboxylate; |
EINECS: | 212-734-0 |
Density: | 1.37 g/cm3 |
Melting Point: | 211 - 216oC |
Boiling Point: | 755.65°C (rough estimate) |
Appearance: | POWDER |
PSA: | 154.10000 |
LogP: | 3.93170 |
Vinblastine (865-21-4) was first isolated by Robert Noble and Charles Thomas Beer from the Madagascar periwinkle plant. Vinblastine's utility as a chemotherapeutic agent was first discovered when it was crushed into a tea. Consumption of the tea led to a decreased number of white blood cells; therefore, it was hypothesized that vinblastine might be effective against cancers of the white blood cells such as lymphoma.
NCI Carcinogenesis Studies (ipr); No Evidence: mouse CANCAR Cancer. 40 (1977),1935. ; (ipr); Clear Evidence: rat CANCAR Cancer. 40 (1977),1935. . EPA Genetic Toxicology Program.
The CAS registry number of Vinblastine is 865-21-4. Its EINECS registry number is 212-734-0. The systematic name is (2α,3α,4α,5β,19β)-vincaleukoblastine. In addition, the molecular formula is C46H58N4O9 and the molecular weight is 810.97. It is also called Vincaleukoblastine. What's more, it is a vinca alkaloid and a chemical analogue of vincristine.
Physical properties about this chemical are: (1)ACD/LogP: 4.18; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 1.73; (4)ACD/LogD (pH 7.4): 3.69; (5)ACD/BCF (pH 5.5): 3.16; (6)ACD/BCF (pH 7.4): 284.81; (7)ACD/KOC (pH 5.5): 16; (8)ACD/KOC (pH 7.4): 1440.47; (9)#H bond acceptors: 13; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 121.24 Å2; (13)Index of Refraction: 1.671; (14)Molar Refractivity: 220.74 cm3; (15)Molar Volume: 590 cm3; (16)Polarizability: 87.5 ×10-24cm3; (17)Surface Tension: 70.9 dyne/cm; (18)Density: 1.37 g/cm3.
Preparation of Vinblastine: it can be prepared by C54H63N5O14. This reaction will need reagent H2, catalyst 10percent Pd/C and solvent methanol. The reaction time is 2 hours at reaction temperature of 25 °C. The yield is about 89%.
Uses of Vinblastine: it can used to treat some kinds of cancer, including Hodgkin's lymphoma, non-small cell lung cancer, breast cancer, head and neck cancer, and testicular cancer. It is also used to treat Langerhan cell histiocytosis. In addition, it can be used to get C46H56ClFN4O8 and C46H56F2N4O8. This reaction will need reagents HF, SbF5 and CHCl3.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(OC)[C@]4(c2c(c1ccccc1n2)CCN3C[C@](O)(CC)C[C@H](C3)C4)c5c(OC)cc6c(c5)[C@@]89[C@@H](N6C)[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@@]7(/C=C\CN([C@@H]78)CC9)CC
(2)InChI: InChI=1/C46H58N4O9/c1-8-42(54)23-28-24-45(40(52)57-6,36-30(15-19-49(25-28)26-42)29-13-10-11-14-33(29)47-36)32-21-31-34(22-35(32)56-5)48(4)38-44(31)17-20-50-18-12-16-43(9-2,37(44)50)39(59-27(3)51)46(38,55)41(53)58-7/h10-14,16,21-22,28,37-39,47,54-55H,8-9,15,17-20,23-26H2,1-7H3/t28-,37-,38+,39+,42-,43+,44+,45-,46-/m0/s1
(3)InChIKey: JXLYSJRDGCGARV-CFWMRBGOBT
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
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human | TDLo | ocular | 14ug/kg (0.014mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE SENSE ORGANS AND SPECIAL SENSES: CONJUNCTIVE IRRITATION: EYE SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE | British Journal of Ophthalmology. Vol. 62, Pg. 97, 1978. |
man | LDLo | intravenous | 2319ug/kg/38W (2.319mg/kg) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION | Lancet. Vol. 2, Pg. 692, 1980. |
man | TDLo | unreported | 80ug/kg (0.08mg/kg) | BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE | Cancer Chemotherapy Reports. Vol. 50, Pg. 219, 1966. |
mouse | LD10 | subcutaneous | 20mg/kg (20mg/kg) | European Journal of Cancer. Vol. 10, Pg. 667, 1974. | |
mouse | LD50 | intraperitoneal | 3120ug/kg (3.12mg/kg) | BLOOD: CHANGES IN BONE MARROW NOT INCLUDED ABOVE IMMUNOLOGICAL INCLUDING ALLERGIC: DECREASED IMMUNE RESPONSE | Cancer Treatment Reports. Vol. 61, Pg. 103, 1977. |
mouse | LD50 | intravenous | 15mg/kg (15mg/kg) | United States Patent Document. Vol. #4279915, | |
rat | LD50 | intravenous | 2mg/kg (2mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1467, 1970. |